Dean Winchester Chronicles
by Superfan4ever
Summary: This is going to be a collection of short stories that will explore Dean Winchester's thoughts and emotions.
1. Pilot

It was a night like any other in the Winchester home. Dean stood on the rail of Sammy's crib to say goodnight. John came home from work just in time to help Mary tuck him into bed. Each night like clockwork Mary would kiss him on the forehead and tell him that angels were watching over him. He snuggled under the covers and drifted off to sleep feeling loved and protected.

This night Dean was awoken to the pounding footsteps of his father down the hall past his room. Then out of the darkness, his screams for Mary. Tromping out of his room, he's met with John handing him Sammy, yelling for him to take his crying baby brother outside.

Confused and scared Dean runs down the stairs and out the front door. In the yard he stands on the lawn staring at the only home he's ever known going up in flames. As he waits for his parents to emerge, he glances down to see his baby brother sound asleep in his four year old arms. This was the moment he knew he was meant to keep his brother safe at all costs. He had no idea at the time what that would actually mean.

Sam had gotten out of the life and into Stanford. Dean was torn about being left alone with John. His emotions ran from angry and disappointed to depressed and lonely. He pushed his feelings down and hunted beside his father for two years. He took on all of John's anger and frustrations. No one will ever know the kind of abuse he endured at the hands of his demon obsessed father.

He knew he was meant for the life of a hunter. He wasn't book smart nor did he care about school, but Sam was smart and deserved a life filled with friends, a girl and a 9 to 5 job. Ultimately he was proud of his brother for pursuing a life outside of hunting, even if he never said it to his face.

When John left Dean to follow a lead on the demon that killed their mother, Dean waited in the dingy motel room he and John shared for days. He paced and worried. Called his father, getting no answer.

Hating the very idea of asking Sam for help, he continued to search on his own to no avail. Along the way he must have dialed Sam's number a thousand times only to hang up before it connected. How, after all this time, could he disturb the life Sam had made for himself at school? But Dean was scared. The little boy inside of him wanted, no needed someone to tell him things would be alright and the only person who could help calm his nerves was his brother. He packed the Impala and drove to Stanford. He needed his little brother and would say or do anything to convince him to come with him to find their father.

He barges into the apartment where Sam lives with Jessica to Dean's surprise. He's hit with the green eyed monster of jealousy. Sam really was living a normal life. One he knew he could never have.

With the promise of an easy job to complete for John and maybe a clue as to his whereabouts was all Sam needed to get on board.

After the woman in white Sam reminded Dean he had to return for his law school interview. He drops him off in front of the apartment building.

To be honest Dean was jealous of the life Sam was building. Sitting in the Impala he tries to think of some excuse to get Sam back. The thought of continuing to search for their dad alone terrified him. Out of the corner of his eye he noticed what could be burning red flames and realized it was and it was coming from Sam's apartment. He ran inside to find Sam yelling at Jessica burning on the ceiling. With speed he pulls Sam out of the apartment and down to the Impala.

The sheer horror in Sam's eyes brings tears to Dean's eyes. Again he was reminded that he has to keep Sammy safe at all costs.


	2. Heart (Season 2 Episode 17)

In the kitchen of Madison's apartment, Dean looked over his brother as he stood with tears streaming down his face. This would be the hardest thing he had ever been asked to do. He would have to kill the woman he loved. Dean could see the way they looked at each other. He felt Sam opening his heart to her and he wanted that for him in a desperate way. To see him happy after all he'd been through the past year, he deserved it. But she was a killer and they couldn't be sure if or when she would kill again. It had to be done.

He begged Sam to let him do it. Not because he wanted the thrill of the kill but because his heart wasn't invested. He could see past the girl to the monster she had become. Sam wouldn't give in, he took the gun and asked Dean to wait.

Time seemed to stand still in that moment. When the shot rang out, Dean's heart stopped. For a few moments his breath was held at the back of his throat. Tears filled his eyes for the pain that Sam would suffer for this.

When Sam returned to the kitchen, he handed Dean the gun and fell into his arms, wracked with grief, his legs giving out. Dean held him tightly as they both dropped to the floor. The sobs coming from Sam were gut wrenching to Dean. All he could do was rock back and forth, holding his baby brother as close as possible.

He wished he could take the pain away. It was his job to watch out for Sammy and again he felt like he failed.


	3. All Hell Breaks Loose (Season 2:22)

Dean sits distraught and angry beside the lifeless body of his baby brother. Tears streamed relentlessly down his face for the better part of three days.

He and Bobby found Sam in a fight for his life. While Bobby chased after Sam's attacker, Dean flew to meet Sam in the mud soaked field, as he fell to his knees. Dean wrapped his arms around his brother, feeling the blood gushing from his back. He had been pierced through with a knife to the lower part of his back, severing his spine. He held Sam against his chest pleading with him to hold on.

Bobby had done his best to comfort Dean, but he was inconsolable to the point of sending Bobby away in anger. Nothing was going to fill the hole that had been created. He had failed at the one thing his father asked of him. The one thing that kept him going was taken from him. What he did know was that he couldn't live with Sam being dead.

"What am I supposed to do, Sammy? What am I supposed to do?!" He screamed.

With nothing but anguish in his heart and mind, he made a decision that would end up having major implications. He left Sam, jumped into his car and sped away to a quiet dirt road and called on a crossroads demon to trade his soul for Sam's life.

He expected to get 10 years like everyone else, but this demon had a grudge against him and wasn't about to make a deal like that with him.

Sam needed to live; he had to carry on with the family business of saving people and hunting things. Dean knew his life was less important in terms of what he had to offer the world on his own.

His father taught him early on in his life that nothing comes before the safety of Sammy. John's words played like a broken record. "Watch out for Sammy."

He accepted one year with the caveat that he not try to get out of it or Sam would die.

When the end came and the hellhounds were barking and he was faced with the reality that was going to Hell, he was not only afraid of what will happen to him downstairs, but more importantly he felt a deep sense of guilt for abandoning Sammy.


	4. When the Levee Breaks (Season 4:21)

Dean watched helplessly as Sam fell deeper under Ruby's spell. She sold him on the lie that he and he alone would stop Lilith from breaking the 66th seal and thus stop Lucifer from rising.

Finding Sam was the easy part as he knew his brother all too well, even though he did his best to stay hidden.

Dean's heart broke as Sam insisted that he was stronger with the blood and Ruby and that it was time for Dean to trust him.

The ensuing battle between them was one of the worst days ever. Rubble littered the motel room where they fought about Ruby and how to kill Lilith.

Dean lies on the floor where he fell after the last punch Sam threw knocked him violently to the floor. His last words were still ringing in his ears.

"You walk out that door, don't you ever come back!"

As he picked himself up and moved to sit on the bed to catch his breath, he held his head in his hands. What the hell was he thinking saying that to Sam? He didn't mean it. The last thing he wanted was for Sam to take on Lilith alone. He certainly didn't trust Ruby and he hated that Sam found it so normal to use his psychic powers. It was all spinning out of control. This was their fight against the angels and the demons. He couldn't wrap his head around the fact that Sam thought he was stronger with Ruby.

Dean never thought of himself as weak. He wasn't afraid of much and was willing to take on anything that came after him or his brother, but this time he wondered if he would have to take on Sam in order to beat Lilith?

Sam inadvertently sets Lucifer free before Dean could stop him. The lies he had been told had caught up to him.

The hate he felt for Ruby burned in him like a wildfire, she had hurt Sam deeply, turning him into the monster he had tried so hard not to becomes, so being able to run her through with his blade was quite satisfying.

He didn't care about the fallout, he would have his brother back and they would deal with whatever came next as a family. The Winchester way.


	5. Apple Pie Life (Season 5:22 Swan Song)

Nothing could have prepared him for this moment. Dean sits on the ground leaning against the Impala. Lucifer has taken over Sam's body. He not only killed Cas and Bobby, but he used his brother's fists to beat him within an inch of his life.

Sam gains control for a few minutes to more or less say goodbye before leaping into the crater set before him, taking Michael and Lucifer with him. Dean's worst fears had just come to fruition, he would have to go on alone.

Although Cas was restored and able to heal his physical injuries, he hurt so deeply that he wanted to die right there in that cemetery.

But he made a promise to Sam. The promise they always told each other. He hated that he was the one left to attempt an apple pie life.

The drive to Lisa's house would be the longest drive of his life. At the door, she welcomed him with open arms and no questions asked. He fell into her arms wracked with sorrow. Again he found himself filled to the brim with a profound anguish that produced more tears than he ever thought possible.

He spent weeks drinking to excess and having horrible nightmares of Sam diving into that damn hole. He wanted his brother back so badly it hurt like a constant stabbing pain in his heart.

They say, time heals all wounds and maybe they're right. Dean spent the better part of that year working on relieving some of his grief, if only to get on with the business of living.

Although he could never fill the empty space that Sam left. He knew he had tried his best to save him but in the end it was Sam who made the decision that would stop the apocalypse and send him to spend unthinkable countless years being Lucifer's vessel.

During this time, to his surprise he learned how to be the father he wanted to be for Ben. He also came to enjoy the way Lisa's eyes lit up when he returned from his construction job. He felt loved and supported with them. He also loved the excitement that Ben showed when he took him to baseball practice. Maybe he could actually live this apple pie life. But then again maybe not.


	6. Soulless Sam (Season 6)

Sam has miraculously returned from Hell and although the person working with Dean looked and sounded like Sam it wasn't fully Sam. Dean struggled to understand what happened to him. He knew that Hell was fraught with horrors that he would rather forget but Sam wasn't sharing his time in the cage and he certainly wasn't his normal doe-eyed, ask questions first, save everyone, self.

He worked twenty-four hours a day, literally. He never slept, because apparently he didn't need to, which was very unsettling. He was ruthless and brutal and that scared Dean to his very core.

Suspicions that something was terribly wrong began to grow when he stood by and allowed Dean to be turned by a vampire. He used him as bait and didn't even bat an eye. The final straw was when the Goddess of Truth said Sam was lying and that scared even her.

Hurting Sam was not exactly what Dean wanted to do, but he had to get a handle on him. He brought Cas in for help.

Cas reluctantly shoved his hand inside Sam's chest. What he found or didn't find startled him.

"Somehow when Sam was resurrected, it was without his soul."

Dean felt like he had been hit by a truck. Those words rattled around in his head for days, making him sick to his stomach.

When Cas informed Dean that putting Sam's soul back even if they were able to find it, could kill him, he was horrified.

Which would be worse? Living with Sam in his current condition or living without him?

He was determined to have his brother back no matter the cost. They could deal with whatever the consequences would be. They always have before and this wasn't going to be any different.

Standing outside the panic room while Death returned Sam's soul to him, sent a shiver through Dean. Sam begging him not to do it and the pained scream that came from him as the beaten and battered missing piece was returned, brought tears to his eyes.

Only time would tell what the consequences would be but for now he was happy to have his brother in tact. Soul and all.


	7. Dean's Final Decision

Dean is poised to kill Sammy. With the scythe in his hands, he prepares to end the nightmare he's been living. According to Death, Sam must be eliminated for him to be free of the mark of Cain.

"Close your eyes, Sammy."

"Wait." Sam pleads with tears streaming down his face. He drops a few old photos on the floor. "Take these. Let them remind you what it was like to love."

Dean glances down at the photos of Sammy as a baby and him with his mom's arms around him. All of a sudden his father's voice fills his thoughts. "Protect Sammy at all costs."

Had he ever really done that? He knows he tried to. Many times he tried, but ultimately, in his mind, he failed. Sure he never gave up on Sam no matter how dire the situation, yet he never felt like he was successful in keeping him safe.

Here he stood on the brink of finally being free of the curse. He would be taken out of the world to live the rest of his life alone. 'Alone' that word bounced around in his head. He hated being alone; even when he needed to be, he honestly hated it. How could he do this? Yes, the mark would no longer be an issue, but the cost felt too high. The weight of what he was about to do pressed in on him.

Death stood behind him, yelling at him to end it. Was it because he was afraid of the so-called darkness or was it revenge for that time Dean convinced Sam to say yes to Gadreel.

What if the tables were turned? Would Sam kill him to save himself? No. He would fight tooth and nail to protect them both.

He stared down at his little brother lying helplessly on the floor, ready to die so that he might be cured. In a blink, Dean makes a decision. One that would have significant consequences, but he would figure it out with Sammy by his side. He swings the scythe. Sam closes his eyes. Dean stabs Death, watching the demon turn to dust before his eyes.

He turns back to a stunned Sam. Taking his hand to help him to his feet.

"You alright?" He asks, realizing the pain he inflicted on Sam.

"I'll live," Sam responds with concern in his eyes. "You?"

"Fan-freaking-tastic! I think I just killed death."

The mark is mysteriously removed by a bolt of lightning. He and Sam rush outside of the old restaurant.

"It's good Dean." He hands him the keys to the Impala. " The mark is gone, and you get your baby back."

Dean stops to look at the keys and over at his beloved car. Then he looks closer at Sam.

Cuts and bruises on Sam's face told the story of a desperate man. He felt the weight of guilt for hurting his baby brother that way. Dean turns his gaze to the dried ground.

"What I did to you in there was selfish and unforgivable and I wouldn't blame you if you never wanted to see me again after this."

Sam bites his lip, a tear drops from his eye. "I wasn't lying when I said you were good, Dean. I know Death had you convinced otherwise, and I was ready to die for you if it meant you wouldn't hurt anyone else. Instead of going through with it, you chose to fight. That's the man I know. The man I am proud to call my big brother."

Sam pulls Dean in for a tight brother hug. Dean hangs on to Sam with all his might. A tear escapes, dripping onto the back of Sam's shirt.

"I'm not going to leave you, Dean," Sam whispers in his ear. He pulls back, holding onto Dean's shoulders. "You and I are in this together, no matter what."

That's just what he needed to hear to face whatever was coming for them, and if Death were right, the darkness would be something worse than anything they had ever encountered. With a new resolve, he smiles and begins to walk toward his baby.


End file.
